Help Me Pull Through
by rawrrry
Summary: With a brand new school year come brand new kids. Rory Gilmore happens to be one of them. What will Chilton have in store for her? A cocky blonde boy, perhaps? Or two?
1. Welcome To Chilton Rory Gilmore

Summary: With a brand new school year come brand new kids. Rory Gilmore happens to be one of them. What will Chilton have in store for her? A cocky blonde boy, perhaps?

**AN: Couple of things you should know: No Dean. Lorelai went to Andover. Luke and Lorelai are together. It makes it so much easier for me; I wouldn't have to write a Luke/Lorelai in the making.**

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Well, this is definitely new. It looked more inviting the last time she saw it. Now it looked more

"…Off with their heads." Lorelai uttered tilting her head to the side.

Rory followed suit and tilted her head at the same angle as her mother's, "Yeah, and more intimidating."

"Are you sure this is Chilton?" The older Gilmore asked, turning to face Rory.

Rory remained looking at the bell tower on the roof and replied, "I'm pretty sure that the 'Chilton' sign and the Chilton uniforms mean that this is Chilton."

"Well, they look like they're smart enough to fool people like us. I bet they sent people to the _real_ Chilton overnight and stole the sign. Then this morning they put arrows that said 'Chilton' on them that pointed to here. And now we're not in Chilton. We're in Hilton!"

"Mom…" Rory started, looking at her mom seriously.

"Okay, okay." Lorelai gave in and moved a stray hair away from Rory's eyes.

They looked at the massive building in front of them and sighed at its intimidation factor. Lorelai stepped out of the car in her blue suit with the flippy skirt, her hair pulled back into a low ponytail and smiled politely at people passing by. Rory pulled her backpack out of the jeep and stepped down onto the gravel road, and rid her skirt of dirt. She walked to her mother's side and looked up, "So, do I look okay?"

Lorelai smiled proudly at her daughter, sixteen years old and a heartbreaker. And she didn't even know it yet. "You look great."

Rory continued to look at her mother and smiled, "You sure?"

Lorelai stepped closer to her daughter and gave her a hug, "I'm sure. Rory, you earned this, you're smart, and pretty and I love you. Now go in there and show them that, just call me if you need anything." She began to walk towards the jeep but was stopped by Rory's demanding voice.

"No, mom. You have to go in there with me and meet Headmaster Charleston."

"Why? You know I have to go back to the inn. Where Michel is. Managing the inn. Alone. When we need to work on the wedding party. Michel. Alone. Are you catching my drift here?"

"Mom! Come on, Michel is fine and Sookie is there. You look great in your flippy skirt and you're not wearing something completely embarrassing so you can come with me." Rory argued pulling her mother through the gates of Chilton.

"But even his name sounds boring and stiff. Headmaster Charleston. It's like Headmaster Erickson all over again." Lorelai muttered as she remembered her own headmaster from Andover.

"Who?" Rory asked as they stopped in front of a massive building.

"My headmaster in Andover. Is this where we're supposed to go?"

Rory pulled out a piece of paper and examined it, "it says we have to go to the Ambroise building."

"Well, is this the Ambroise building?"

"Possibly." Rory examined the piece of paper again and began to flip it around.

Lorelai cast an incredulous look at her daughter, "you don't even have the map on the right direction."

Rory bit her lip and stuck her tongue out a bit, "Wait…" She continued in turning the piece of paper that had no writing but black and white boxes in it. "Stupid map. It doesn't even have names on the buildings."

"What kind of map is that?" Lorelai asked peering over at the paper. "That's not a map, that's a freaking get lost guide."

Rory gave up in trying to figure out the workings of the map and stuffed it in her bag. "How are we supposed to get to Headmaster Charleston, now?"

Lorelai smiled brightly, "I guess we won't have to then. I'll see you later sweets." Lorelai turned around and immediately bumped into a passing brunette. "Oh, sorry love."

"Whoa. Make a noise next time." Lorelai uttered as she picked up her purse that fell to the ground.

She looked up to find the brunette walking away, "sorry again love. Hey guys! Wait up!"

"Well, good to know that you're going to have great classmates here Rory."

"Yes, they're the exact epitome of polite." Rory deadpanned. "Come on mom, let's ask someone where the Ambroise building is."

"At least we know that they have sexy accents here." Lorelai commented as Rory pulled her arm.

"What?"

"Did you not notice the sexy accent?" Lorelai asked disbelievingly. "My own daughter disappoints me. Shame."

Rory rolled her eyes only slightly, "Yeah, shame." She wandered over to the nearest Chilton student. "Excuse me." She patted the girl's shoulder.

The girl turned around her facial features giving away the fact that she was _not_ happy of being interrupted. She had long straight blonde hair and held on to her single-strap messenger bag with ferocity. "What?" She barked at Rory.

Rory was a bit taken aback at the girl's attitude. First, some impolite guy who bumped into people and now a blonde who looked like she was ready to pounce. Chilton sure was turning out to be a great school and learning environment. "Uh- I was just wondering if you knew where the Ambroise building is."

The blonde gave her a look over and scoffed, "Do I look stupid?" She didn't wait for Rory's answer, "No, I'm not stupid. I know where the Ambroise building is." She turned away, ignoring Rory and focused her attention on another blonde and raven-haired girl.

Lorelai was appalled at the nerve of this girl. _How dare she?_ "Excuse me." Lorelai asked with certainty in her voice.

The blonde whirled around once again and gave Lorelai an unwanted look, "what?" She noticed that she was speaking to an older woman instead of the younger one and gave her a look over. "You're not supposed to be on school grounds. You don't have a uniform and I'm assuming you don't go here."

Now, Lorelai was annoyed, "Hey, we're just asking a question –"

"And I answered it already. I know where the Ambroise building is."

"Well then where is it?" Lorelai asked impatiently tapping her foot.

"You could've just asked that in the first place." The blonde smirked and pointed out. Instead of answering she walked away but not before she stated, "Madeline, tell them where it is."

The two Gilmores stared after the blonde and watched as the raven-haired girl, apparently known as Madeline, walked up to them, "Forgive Paris. She's just…well… Paris. The Ambroise building is right behind you." Madeline strutted away with a small wave.

"That was…" Lorelai began.

Rory finished her thought, "interesting."

"Interesting." Lorelai nodded in agreement. "You're going to make the _greatest_ here. I can just tell." She smiled at her daughter and placed her arm around Rory's shoulder as they went back to the building where they were minutes ago.

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"Here is your schedule, your locker number and combination, the map of Chilton, the rules, the Chilton Honor code and the school song which must be recited upon demand and if you do it in Latin, you get extra credit. Welcome to Chilton." The lady, known as Mrs. James, welcomed in a raspy voice.

Rory thanked her and looked down at the pieces of paper, all of which were printed in Chilton stationeries, and took a deep breath in. She noted that her first class was English with Mr. Max Medina in room twelve then she looked at her map and looked for room twelve. "On the other side of school, great." She muttered before stepping out of the office and into the marble halls of Chilton Preparatory.

The bell still hadn't rung yet so she decided to stop by her locker. _Locker number one hundred fourteen._ Rory noticed as the numbers on the lockers gradually became higher until she finally got to locker number one hundred- _what?_ Low and behold was a blonde boy pushing some girl against locker… one hundred twelve probably. And just a few feet from that blonde boy was another blonde boy making out with another girl – at least this one didn't have the girl pushed up against the lockers. Rory noticed that her locker was in the gap between the two blondes and she slowly reached for the lock with one hand, and held up her locker combination with the other. She opened it and placed some of the books that were in her bag into the locker and was about to close it when she heard a familiar voice with a heavy accent, "Huntz! Dugrey!"

Another boy, brown haired with a more business-like look to him, was behind him and shouted out, "Tristan! Logan!"

A blonde girl, who had her arms wrapped around the brunette, rolled her eyes at the two blonde boys. "Break it up already."

The first blonde boy – the taller one, Rory noticed - broke off with the girl he was with and ruffled his hair. "I got to go," he said to the girl he was making out with just a few seconds ago.

The girl giggled, "okay. Bye Tristan."

"Bye Summer. I'll see you after class." The blonde, apparently know as Tristan, said.

"Definitely." Summer giggled again and gave Tristan a parting kiss.

Tristan watched as Summer walked off in the other direction, glanced at Rory before dismissing her and focusing his attention on the other blonde boy who must be Logan. "Logan, man."

Logan broke off from the girl and gave her a grin. The girl giggled in an all too high-pitched voice, "bye Logan."

"Yeah, bye-" He seemed to have forgotten her name and coughed or was it cleared his throat as to say her name, "ehemurgh."

She waved as she walked away with a certain sway and with a parting giggle she disappeared into the other hall. Logan diverted his attention away from the girl and focused on his group but not before he gave Rory a smirk and a "hey."

Before she could even utter a word, the boy with the accent launched into a story about his father finding him naked in the study. Just then, the bell rang and the group separated into two directions. Rory closed her locker and her bag then took out her map. _Room twelve, English with Mr. Max Medina._ She strolled over to her classroom, hoping she wouldn't be late and got there just as the bell rang. Not knowing where to sit, and whether or not she was supposed to be assigned a seat, Rory stood by the door and waited for Mr. Max Medina to walk in.

"Well, hello there. I'm assuming you're the new student from Stars Hollow High Headmaster Charleston was talking about." A man clad in a suit with a case in one hand, asked.

Rory nodded in confirmation, "Yes, I'm Rory Gilmore."

"Alright, well, I'm Mr. Medina." He looked down on a sheet of paper, "I don't have a Rory Gilmore in this class. I have a Lorelai Gilmore but not a Rory Gilmore."

"Oh, Rory is my nickname."

"So, that's what you would like to be called? Not Lorelai?" Mr. Medina asked.

Rory answered, "Yes."

"Wonderful," Mr. Medina replied as he jotted down 'Rory' on the piece of paper. He faced the class and cleared his throat and once everyone was seated and his attention he announced, "class we have a new student. Say hello to Rory Gilmore. She just transferred from Stars Hollow High and I would like you to give her a warm welcome."

The obligated response came. "Hello Rory."

_Welcome to Chilton Rory Gilmore.

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**AN: Review. :)**


	2. Want To Join Our Group?

AN: Finally, midterms are over. So, I know in the show that Rory goes to Chilton for sophomore year. She comes in junior year in this story. :)

And in advance, I apologize to those who are named Summer.

Thanks for such great response!

Disclaimer: Wow, I still don't own anything. SHOCKER.

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Mr. Medina looked around the room, gazing for an open seat. _Bingo!_ _But why is _that_ seat empty?_ Pushing his confusing thoughts aside, he instructed Rory, "Ms. Gilmore, have a seat right in between Mr. Dugrey and Mr. Huntzberger.

Tristan, who was previously looking at something outside the window, suddenly sat up straight and looked at his teacher, "Sorry Mr. Medina, I forgot it this morning."

Logan, sitting just two seats away from Tristan, also looked away from the girl he was eyeing and looked at Mr. Medina, "Oh, I didn't know we were assigned something Mr. Medina. I'm terribly sorry."

Stifling a giggle, Stephanie Vanderbilt, sitting behind the empty seat between Tristan and Logan, stared at two of her friends and whispered, "Is that your final answer?"

Tristan and Logan both glanced at Stephanie with confusion then turned their heads to a waiting Mr. Medina, "I'm sure you two boys could turn in whatever you forgot this morning or didn't hear, tomorrow. But right now, I'm just telling Ms. Gilmore here to sit in that empty seat between the two of you."

The two boys gave him an understanding look before focusing their attention on the innocent looking girl. She walked to her newly assigned desk without even trying to add a jaunt in her step. Yet, she managed to have it there anyway. Her plaid Chilton skirt came to an end right at her knees and just one button of her blouse was left open – one button that was in no way revealing.

Rory sat down on her new desk, already paying attention to what Mr. Medina was saying about a new in-class project. She readily took out her new notebook – bought for this special first day – and scribbled notes that weren't mandatory at all.

To Tristan Dugrey, she looked like a Mary being all studious and innocent.

To Logan Huntzberger, Miss Rory Gilmore looked like an Ace Reporter with her pen moving hastily across her notebook at an incredible speed.

To every other girl in the room, aside from Stephanie, she was a threat. Sitting unbelievably close to the two Kings of Chilton, this girl was a slut in disguise.

"So go ahead and get into groups of four for this project." Mr. Medina instructed.

"I pick Tristan and Logan." Stephanie simply stated smiling at both of her friends. "Okay, we need one more."

"How about…" Logan looked around, looking for someone he hadn't slept with… yet.

Stephanie looked at Logan, "Not one of your one night stands, Logan." She then turned to Tristan, "And not one of your exes." Stephanie warned not wanting to see some girl try to get into Dugrey or Huntzberger's pants.

The two boys leaned back and sighed, a small smirk plastered on their faces, muttering, "I guess that leaves out basically every girl in this room."

Stephanie rolled her eyes at the last comment and set her eyes on the person sitting right in front of her. "Hey," _name, name, what was her name?_ "Rory. Hey, want to join our group?"

Rory turned to see the one who offered her a spot in their group. She gave the blonde a smile, "Sure." She rotated her desk so it faced Stephanie's and smiled.

"I'm Stephanie." She held out her hand with a smile.

Rory gladly took it and shook her hand, "I'm Rory."

Upon hearing Stephanie talk to another girl, possibly their last group member, Tristan and Logan averted their eyes from some girls winking at them. They were suddenly met with the sight of Rory Gilmore amicably talking to Stephanie.

"Where's Stars Hollow?"

"Not too far. About half an hour or so."

Stephanie tilted her head to the side, "huh, I've never heard of it."

"It's pretty small."

"Do you like it there?"

Rory smiled, her blue eyes twinkling, making them stand out more, "Of course."

Tristan adjusted his seat so it was right next to Rory's and facing Stephanie, "Hey Mary."

"It's Rory, you dimwit." Stephanie shot back.

Tristan shook his head pointing at Stephanie, "I don't think I was talking to you, was I Steph? I was talking to Mary here."

"Rory." Stephanie corrected once again.

"So Ace, I noticed you took some notes." Logan began, positioning his chair by Rory and inching closer to her until their arms touched, pretending to look at the notes she took.

_What was up with the nicknames?_ Rory looked into his deep chocolate brown eyes that held mischief, "It's Rory. R-O-R-Y, Rory." She stated getting annoyed.

"Well I'm Logan. Logan," He paused, knowing this was when girls would fall for him even deeper than they previously were, "Huntzberger."

"That's great Logan Huntzberger but try to learn my name first." Rory said dryly, her patience for the two blonde boys growing short.

Logan tried to pick up a new conversation, "So why are you here?"

Definitely getting impatient, Rory replied dryly, "It's a Monday and the law states that I need to go to school."

Tristan chuckled at how Rory easily brushed off one of his friends, "Mary, what are you doing tonight?"

Stephanie sighed, "You have a girlfriend, Tristan. Summer. Does the bitchy name ring a bell or what?"

Ignoring the insult on his girlfriend, Tristan raised both hands in mock surrender, "What? I was just wondering what she was doing tonight. You know, to start on this project."

"We really should start on the project now." Rory said looking at the set of guidelines she had recorded.

"See?" Tristan pointed out, "I vote my place."

"It's an in-class assignment." Logan answered rolling his eyes.

"Oh." Tristan accepted defeat and slumped down on his chair.

"Yeah, oh." Stephanie nodded and instructed the boys to read through the guidelines that Rory took notes on.

Rory took out the literature book and began her trek to look for the correct page when Stephanie, in a perky voice, inquired, "So what's your schedule?"

Looking up from the book, Rory said, "pardon?"

"Your schedule."

Rory reached into her left pocket and retrieved a folded sheet of paper. Stephanie took it in one swift motion and looked at it.

_1. English – Mr. Medina_

_2. Biology – Mrs. Smith_

_3. Gym – Mr. Johnson_

_4. Calculus – Mr. Stevenson_

_5. History – Mrs. Laurel_

_6. Spanish – Mr. Gomez_

"Good schedule." Stephanie deduced.

Rory nodded slowly, "Thanks…"

"What's it like?" Logan asked, "any more classes that I share with the gorgeous Rory Gilmore?"

"I don't think she really wants to see you in another class Logan." Tristan said spinning the pen in his hand. "But me, however..."

"I highly doubt that. If it was a choice between the two of us, she'd choose me in a heartbeat." Logan responded giving Rory a smirk.

Stephanie looked at Rory's schedule again, glancing up every now and then, "Well, obviously, you have English with the two pretty playboys and I."

Logan and Tristan both gave Rory and award-winning grin, and then turned to Stephanie, "We're _pretty_ playboys, now?"

"You don't usually associate the word 'pretty' with boys unless 'pretty' is an adjective for a girl a boy is with." Tristan said, "I'm not sure I want to be called 'pretty'. Sends a mixed message."

"You sure the message isn't true?" Logan asked smirking.

Stephanie sighed, "I use the word 'pretty' lightly. It means attractive. Look it up."

"Hear that? We're attractive." Tristan said.

"Yeah, I bet that's news to you." Logan replied smirking.

Continuing, Stephanie rolled her eyes at the childish actions, "So English with Stephanie and the playboys. That last word, I don't use lightly. Anyways, Biology you have with Tristan and his girlfriend of the month Summer."

"Glad to know you have such faith in our relationship Steph." Tristan quickly said.

She gave him a look portraying innocence, "what? You were hitting on Rory until I reminded you of the whore."

Rory gave Stephanie a short glance, "I'm thinking you hate her."

Stephanie leaned in closer, whispering, "She is such a bitch. Like last week- ugh. I don't even want to waste my breath on her." She leaned back again and continued with going over Rory's schedule. "Alright, Gym you have with Logan, Tristan, Colin, Finn and I. So that's basically all of us. That will be fun. No one in your calculus class, though. History, you have with Colin. He's mine." Stephanie smiled then persisted, "He's part of our little group. I'll tell him to look out for you.

Rory smiled, "thanks."

"Fortunately for you Finn is also in you History class. He's… how do I say this? He's…" she tried to search for a word that might describe Finn but failed miserably, "you'll find out. Then you've got Spanish with…" She seemed to be stuck for a moment and turned to Logan, "who has Gomez sixth?"

"Me." Logan answered smirking as he slung his arm around Rory's shoulder. "_Hola mi bonita."_

"Smooth, Logan." Tristan commented.

Unable to concentrate with Logan's arm on her shoulder (really, who would?), Rory hesitantly shrugged it off, causing Logan to frown and Tristan to chuckle. Rory said, "Okay, back to work. I'm not sure I want a failing grade for my first project here."

The group began their project, Tristan and Logan stealing looks at Rory as she read the required steps and Stephanie occasionally unleashing some interesting facts about her and her friends.

The bell rang and Mr. Medina announced, "Have a great day! Don't forget to do some extra research on your projects, it will help out greatly in the end."

Rory picked up her belongings and gave Stephanie a small, thankful smile for making her first day a bit easier, "So I guess I'll see you in Gym during third period?"

"Right-o." Stephanie replied happily, waving as she walked out of the classroom.

"Bye Ace." Logan winked giving Rory a light touch on the arm.

"Rory." She corrected, "Learn to say it right Huntzberger."

"I'll see you later." He said before walking out with a grin.

A group of girls passed, sending Rory the dirtiest looks she had ever received.

"Bitch." One muttered as she passed by, not right out saying it in her face but intending for Rory to hear.

"Whore." Another spat.

"Slut." One said with a death glare.

"A Mary? Yeah right. She's just trying to get Logan and Tristan's attention." A girl scoffed.

"Wait until Summer hears about her. That will send this girl running back to her old school." The last one said, emitting snickers from the others.

_What was up with these girls?_ Rory heard herself ask as she picked up her belongings faster. She was appalled. Completely astounded at what these girls would dare say about her, knowing she could hear them. And it was her first day? Enemies on her first day? Yeah, she was going to make the best of friends here.

She began to walk though the halls of Chilton looking for her Biology class when suddenly, out of nowhere, she felt an arm place itself on her shoulder. "Don't worry about those girls. They just want attention from the hottest guy in school. Namely, me." Tristan smirked, winking at Rory.

Rory ducked out from his embrace and grinned, "Correct me if I'm wrong but I heard Logan's name also and I'm pretty sure he was mentioned first, you last." She entered a classroom, which she correctly assumed as her Biology class with Tristan still trailing behind her.

"Well, you know what they say about saving the best for last." Tristan said with a parting grin before they both heard a short squeal.

The same brunette from earlier in the morning, by the lockers, came sauntering over to Tristan and made sure to sway a bit as she passed a group of boys calling out to her. She ignored said guys but grinned at knowing she could entice them, and walked straight up to Tristan, her arms immediately finding its way to his neck. She leaned up to capture his mouth into a passionate kiss and the two stayed in the embrace until Mrs. Smith came strolling in.

"Mr. Dugrey. Ms. Chatsworth. I'm sure there are other places for such behavior but I assure you that my classroom is not one of them. Take your seats." With smirks on their faces, Tristan and Summer walked to their seats, conveniently located in the far corner of the class.

Mrs. Smith glanced at Rory and said, "I don't think I've seen you before. Are you a new student?"

"Yes Ma'am." Rory answered politely.

"Name?"

"Lorelai Gilmore but I go by Rory."

"Fortunately for you, since Robert dropped out just a week ago, there's a student in need of a lab partner. Ms. Gilmore, your lab partner will be Ms. Gellar." Mrs. Smith said pointing to the lab table by the window in the second row.

_Oh goody. _Rory thought as she approached the same girl she had tried to ask directions from earlier.

"You've got to be kidding me." The girl muttered.

Taking a deep breath in, Rory decided that it would be best if she introduced herself, "Hi. I'm Rory."

The girl turned her head to look at Rory straight in the eye, "Look, Rory, I'm Paris and I'm not here to sit around and gossip about who kissed who last Saturday night at the party. I'm here to learn so I can get to a good college. If you'd rather flirt with the male species go ahead and waste your life and ruin your grade but you are not bringing me down with you so get to work."

_That was a warm greeting.

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AN: Review. :) Please?


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